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Both Sides of the Table: What Buying and Selling Businesses Taught Me

Published July 7, 2026

Pedro Oliveira, Founder & Principal, Renova Strategy

A personal note from our founder.

Most people who advise on business sales have never actually sold a business they built. Fewer still have been the buyer. I have done both: I built and sold multiple businesses, and I acquired, grew, and sold a technology services company that someone else had started. Sitting on both sides of the table changed how I see every deal, and I want to share the lessons that only doing both can teach.

Sellers price effort. Buyers price risk.

This is the single biggest gap in every negotiation, and I have felt it from both chairs.

As a seller, I knew what the business had cost me. The years, the missed weekends, the payroll I covered personally in the hard stretches. All of that felt like it should be in the price. It is not. None of it is in the price. The buyer was not there for any of it, and they are not buying your history. They are buying your future cash flow, discounted by everything that could go wrong with it.

As a buyer, I learned the other half. When I evaluated the company I eventually acquired, I was not asking what the owner had put in. I was asking: what happens to these clients when he leaves? Which of these numbers survive contact with reality? What am I not being told? Every unanswered question became a deduction in my head.

If you are preparing to sell, understand this: every risk you leave unaddressed, the buyer will price. Usually silently, and usually more harshly than you would.

The business you know is not the business you can sell

When I sold, I discovered how much of the company lived in my head. Client quirks, pricing logic, why we did things a certain way. To me it was obvious. To a buyer it was undocumented risk.

When I bought, I inherited the mirror image: a business where the previous owner’s knowledge walked out the door on closing day, and I spent the first year rediscovering things he could have written down in an afternoon.

The lesson cuts both ways. Documentation is not paperwork. It is transferable value. It is the difference between selling a business and selling yourself a job you are about to quit.

The best deals are boring

The transaction I remember most fondly was the least dramatic one. Clean books, honest disclosure, realistic expectations on both sides, and a structure where nobody was trying to win the last dollar. It closed on schedule and both sides would do it again.

The deals that nearly died all shared the same features: surprises in diligence, numbers that shifted, and one side treating negotiation as combat. Surprises kill deals. Not because the underlying facts are always fatal, but because a surprise tells the buyer there may be more surprises.

Why this shapes how we advise

At Renova Strategy, this experience is the foundation of the practice. When we tell a seller their add-back will not survive diligence, it is because we have been the buyer striking it out. When we tell a buyer a seller’s price is defensible, it is because we have built what they are trying to buy.

There is no substitute for having signed on both lines.

If you are thinking about a sale or an acquisition and want an advisor who has lived both sides, let’s talk. An initial consultation is free.